> A section of the stack trace is at the end of this email. Crash is really in core Emacs (re-display engine may be?) triggered by Org related things.
It is worth disabling font-lock in Org buffers. I am not sure whether that would prevent you from making use of any of the Org features. If you could bisect the Org file and narrow down the crash to a smaller example file that would be wonderful. Can you give us an idea of number of scheduled entries per day and how many months they typically span. I know Org uses cache so may be the performance hit is one time only. May be there could be a script that populates the cache as part of first step in the migration process. Btw, I find the use of "theoretically" a bit inconsistent in your email. As a developer myself, I wouldn't go to the extent of a writing a migration assistant just to reap purely "theoretical" benefits. Surely I am nitpicking here. Jambunathan K.